4-Methyl-N-(4-oxo-2-thioxoimidazolidin-3-yl)-1,2,3-thia­diazole-5-carboxamide

The mol­ecule of the title compound, C₇H₇N₅O₂S₂, is non-planar. The dihedral angles formed by the thio­hydantoin and methyl­thia­diazole systems with the amide group are 85.5 (1) and 38.4 (3)°, respectively. The crystal structure is stabilized by inter­molecular N—H...N/O hydrogen bonds and short S...O contacts, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.151
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.91

Author Response: Data collection was stopped because too many low reflecions

Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: KM-4 Software (Kuma, 1991); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

4-Methyl-N-(4-oxo-2-thioxoimidazolidin-3-yl)-1,2,3-thiadiazole-5-carboxamide

Crystal data

C7H7N5O2S2	F(000) = 528
Mr = 257.30	Dx = 1.581 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 66 reflections
a = 7.528 (2) Å	θ = 6–21°
b = 7.239 (1) Å	µ = 4.46 mm^−1
c = 19.843 (4) Å	T = 293 K
β = 91.74 (3)°	Prism, orange
V = 1080.8 (4) Å^3	0.6 × 0.4 × 0.1 mm
Z = 4

Data collection

Kuma KM-4 four-circle diffractometer	1640 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
Graphite monochromator	θmax = 75.1°, θmin = 5.9°
ω–2θ scans	h = −9→9
Absorption correction: for a sphere (Dwiggins, 1975)	k = −9→0
Tmin = 0.035, Tmax = 0.135	l = −24→0
2227 measured reflections	3 standard reflections every 100 reflections
2184 independent reflections	intensity decay: 0.5%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: geom, difmap
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.151	w = 1/[σ^2(Fo^2) + (0.1205P)^2 + 0.0129P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2184 reflections	Δρmax = 0.62 e Å^−3
147 parameters	Δρmin = −0.46 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0078 (13)

Special details

Experimental. Interpolation using Int·Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0–2.5, and Int·Tab. Vol·II (1959) p.302; Table 5.3.6 B for muR in the range 2.6–10.0. The interpolation procedure of C·W·Dwiggins Jr (Acta Cryst.(1975) A31,146–148) is used with some modification.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.40296 (8)	0.88715 (11)	0.23310 (3)	0.0589 (3)
S2	0.16190 (10)	0.77031 (10)	0.52810 (4)	0.0611 (3)
N1	0.1102 (3)	1.0270 (3)	0.21317 (10)	0.0529 (5)
N2	0.2606 (3)	1.0047 (4)	0.18480 (10)	0.0617 (6)
N3	0.1770 (3)	0.6448 (3)	0.37863 (9)	0.0486 (5)
H3N	0.0654	0.6187	0.3537	0.058*
N4	0.2197 (3)	0.5225 (3)	0.42979 (9)	0.0453 (4)
N5	0.2779 (3)	0.4195 (3)	0.53043 (10)	0.0510 (5)
H5N	0.3114	0.3946	0.5782	0.061*
O1	0.4569 (2)	0.7610 (3)	0.38045 (10)	0.0641 (5)
O2	0.2900 (3)	0.2754 (3)	0.36300 (10)	0.0680 (6)
C3	0.2570 (3)	0.8608 (3)	0.29453 (10)	0.0415 (4)
C4	0.1011 (3)	0.9481 (3)	0.27579 (11)	0.0438 (5)
C5	−0.0622 (4)	0.9758 (4)	0.31469 (15)	0.0622 (7)
H5A	−0.0777	1.1051	0.3235	0.075*
H5B	−0.0512	0.9101	0.3566	0.075*
H5C	−0.1631	0.9301	0.2891	0.075*
C6	0.3095 (3)	0.7533 (3)	0.35556 (11)	0.0434 (5)
C7	0.2779 (3)	0.3437 (3)	0.41777 (12)	0.0478 (5)
C8	0.3167 (3)	0.2659 (3)	0.48672 (13)	0.0524 (6)
H8A	0.2409	0.1609	0.4957	0.063*
H8B	0.4401	0.2283	0.4919	0.063*
C9	0.2204 (3)	0.5691 (3)	0.49736 (11)	0.0428 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0498 (4)	0.0765 (5)	0.0508 (4)	−0.0032 (3)	0.0062 (2)	0.0138 (3)
S2	0.0672 (5)	0.0522 (4)	0.0644 (4)	−0.0014 (3)	0.0091 (3)	−0.0118 (3)
N1	0.0653 (12)	0.0492 (11)	0.0435 (10)	−0.0006 (9)	−0.0104 (8)	0.0081 (8)
N2	0.0722 (13)	0.0692 (14)	0.0436 (11)	−0.0072 (11)	−0.0019 (9)	0.0143 (9)
N3	0.0542 (10)	0.0504 (10)	0.0404 (9)	−0.0057 (8)	−0.0114 (7)	0.0120 (8)
N4	0.0560 (10)	0.0436 (9)	0.0359 (8)	0.0009 (8)	−0.0053 (7)	0.0067 (7)
N5	0.0580 (11)	0.0525 (10)	0.0420 (9)	0.0007 (9)	−0.0071 (8)	0.0066 (8)
O1	0.0452 (9)	0.0848 (14)	0.0615 (11)	−0.0001 (8)	−0.0121 (8)	0.0212 (9)
O2	0.0859 (14)	0.0650 (11)	0.0533 (10)	0.0002 (10)	0.0075 (9)	−0.0161 (8)
C3	0.0445 (10)	0.0451 (10)	0.0348 (9)	−0.0027 (8)	−0.0025 (7)	0.0018 (8)
C4	0.0519 (12)	0.0390 (10)	0.0398 (10)	0.0008 (8)	−0.0081 (8)	0.0010 (8)
C5	0.0636 (15)	0.0564 (15)	0.0667 (16)	0.0172 (12)	0.0058 (12)	0.0053 (12)
C6	0.0441 (11)	0.0468 (11)	0.0389 (10)	0.0035 (8)	−0.0036 (8)	0.0031 (8)
C7	0.0476 (11)	0.0457 (11)	0.0501 (11)	−0.0031 (9)	0.0022 (9)	−0.0020 (9)
C8	0.0522 (12)	0.0468 (12)	0.0575 (14)	0.0014 (9)	−0.0062 (10)	0.0060 (9)
C9	0.0408 (9)	0.0478 (10)	0.0395 (10)	−0.0065 (8)	−0.0019 (7)	0.0013 (8)

Geometric parameters (Å, º)

S1—N2	1.652 (2)	N5—H5N	0.9900
S1—C3	1.676 (2)	O1—C6	1.202 (3)
S2—C9	1.644 (2)	O2—C7	1.200 (3)
N1—N2	1.290 (3)	C3—C4	1.374 (3)
N1—C4	1.371 (3)	C3—C6	1.483 (3)
N3—C6	1.360 (3)	C4—C5	1.485 (3)
N3—N4	1.378 (2)	C5—H5A	0.9600
N3—H3N	0.9799	C5—H5B	0.9600
N4—C9	1.382 (3)	C5—H5C	0.9600
N4—C7	1.389 (3)	C7—C8	1.500 (3)
N5—C9	1.332 (3)	C8—H8A	0.9700
N5—C8	1.446 (3)	C8—H8B	0.9700
N2—S1—C3	93.02 (11)	H5A—C5—H5B	109.5
N2—N1—C4	114.3 (2)	C4—C5—H5C	109.5
N1—N2—S1	111.94 (16)	H5A—C5—H5C	109.5
C6—N3—N4	117.48 (18)	H5B—C5—H5C	109.5
C6—N3—H3N	124.6	O1—C6—N3	124.5 (2)
N4—N3—H3N	115.2	O1—C6—C3	122.1 (2)
N3—N4—C9	123.5 (2)	N3—C6—C3	113.44 (19)
N3—N4—C7	122.68 (19)	O2—C7—N4	124.9 (2)
C9—N4—C7	113.69 (18)	O2—C7—C8	130.8 (3)
C9—N5—C8	113.49 (19)	N4—C7—C8	104.3 (2)
C9—N5—H5N	133.6	N5—C8—C7	102.75 (19)
C8—N5—H5N	112.6	N5—C8—H8A	111.2
C4—C3—C6	131.8 (2)	C7—C8—H8A	111.2
C4—C3—S1	108.90 (15)	N5—C8—H8B	111.2
C6—C3—S1	119.30 (16)	C7—C8—H8B	111.2
N1—C4—C3	111.8 (2)	H8A—C8—H8B	109.1
N1—C4—C5	118.7 (2)	N5—C9—N4	105.7 (2)
C3—C4—C5	129.4 (2)	N5—C9—S2	128.63 (18)
C4—C5—H5A	109.5	N4—C9—S2	125.63 (17)
C4—C5—H5B	109.5
C4—N1—N2—S1	−0.5 (3)	C4—C3—C6—N3	38.2 (3)
C3—S1—N2—N1	0.9 (2)	S1—C3—C6—N3	−140.75 (19)
C6—N3—N4—C9	86.1 (3)	N3—N4—C7—O2	−3.1 (4)
C6—N3—N4—C7	−89.4 (3)	C9—N4—C7—O2	−179.1 (2)
N2—S1—C3—C4	−1.04 (17)	N3—N4—C7—C8	177.3 (2)
N2—S1—C3—C6	178.12 (19)	C9—N4—C7—C8	1.3 (2)
N2—N1—C4—C3	−0.3 (3)	C9—N5—C8—C7	1.3 (3)
N2—N1—C4—C5	176.2 (2)	O2—C7—C8—N5	179.0 (3)
C6—C3—C4—N1	−178.1 (2)	N4—C7—C8—N5	−1.5 (2)
S1—C3—C4—N1	0.9 (2)	C8—N5—C9—N4	−0.5 (3)
C6—C3—C4—C5	6.0 (4)	C8—N5—C9—S2	179.74 (17)
S1—C3—C4—C5	−175.0 (2)	N3—N4—C9—N5	−176.5 (2)
N4—N3—C6—O1	−6.7 (4)	C7—N4—C9—N5	−0.5 (3)
N4—N3—C6—C3	171.90 (19)	N3—N4—C9—S2	3.3 (3)
C4—C3—C6—O1	−143.2 (3)	C7—N4—C9—S2	179.19 (17)
S1—C3—C6—O1	37.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···N1^i	0.98	1.96	2.912 (3)	163
N5—H5N···O1^ii	0.99	2.21	2.933 (3)	129
N5—H5N···N2^iii	0.99	2.28	3.118 (3)	142

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+3/2, z+1/2.